ES2211232T3 - Solvatos mixtos de paroxetina-propan-2-ol. - Google Patents

Solvatos mixtos de paroxetina-propan-2-ol.

Info

Publication number: ES2211232T3
Authority: ES; Spain
Prior art keywords: propan; solvent; solvate; transformation; acetone
Prior art date: 1998-11-30
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

ES99973027T

Other languages

English (en)

Spanish (es)

Inventor

Andrew Simon Smithkline Beecham Pharma. Craig

Victor Witold Smithkline Beecham Pharm. Jacewicz

Neal Smithkline Beecham Pharmaceuticals Ward

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

SmithKline Beecham Ltd

Original Assignee

SmithKline Beecham Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-11-30

Filing date

1999-11-30

Publication date

2004-07-01

1998-11-30 Priority claimed from GBGB9826182.9A external-priority patent/GB9826182D0/en

1999-07-12 Priority claimed from GBGB9916257.0A external-priority patent/GB9916257D0/en

1999-11-30 Application filed by SmithKline Beecham Ltd filed Critical SmithKline Beecham Ltd

2004-07-01 Application granted granted Critical

2004-07-01 Publication of ES2211232T3 publication Critical patent/ES2211232T3/es

2019-11-30 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000012453 solvate Substances 0.000 title claims abstract description 59
AHOUBRCZNHFOSL-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidine Chemical compound C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 claims abstract description 125
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 84
229960005183 paroxetine hydrochloride Drugs 0.000 claims abstract description 52
239000002904 solvent Substances 0.000 claims abstract description 36
239000000203 mixture Substances 0.000 claims abstract description 33
230000009466 transformation Effects 0.000 claims abstract description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 18
238000010438 heat treatment Methods 0.000 claims abstract description 18
150000002148 esters Chemical class 0.000 claims abstract description 5
150000002576 ketones Chemical class 0.000 claims abstract description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 4
150000002825 nitriles Chemical class 0.000 claims abstract 4
150000008280 chlorinated hydrocarbons Chemical class 0.000 claims abstract 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 114
238000000034 method Methods 0.000 claims description 40
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 claims description 21
229960002296 paroxetine Drugs 0.000 claims description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
239000013078 crystal Substances 0.000 claims description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
239000000725 suspension Substances 0.000 claims description 11
208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 10
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 8
238000004807 desolvation Methods 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 7
206010036618 Premenstrual syndrome Diseases 0.000 claims description 6
238000002425 crystallisation Methods 0.000 claims description 6
230000008025 crystallization Effects 0.000 claims description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 5
230000002265 prevention Effects 0.000 claims description 5
208000007848 Alcoholism Diseases 0.000 claims description 3
208000024827 Alzheimer disease Diseases 0.000 claims description 3
208000019901 Anxiety disease Diseases 0.000 claims description 3
208000032841 Bulimia Diseases 0.000 claims description 3
206010006550 Bulimia nervosa Diseases 0.000 claims description 3
208000019695 Migraine disease Diseases 0.000 claims description 3
208000008589 Obesity Diseases 0.000 claims description 3
208000002193 Pain Diseases 0.000 claims description 3
206010039966 Senile dementia Diseases 0.000 claims description 3
206010041250 Social phobia Diseases 0.000 claims description 3
238000013019 agitation Methods 0.000 claims description 3
201000007930 alcohol dependence Diseases 0.000 claims description 3
208000022531 anorexia Diseases 0.000 claims description 3
230000036506 anxiety Effects 0.000 claims description 3
238000001816 cooling Methods 0.000 claims description 3
206010061428 decreased appetite Diseases 0.000 claims description 3
208000024732 dysthymic disease Diseases 0.000 claims description 3
238000001802 infusion Methods 0.000 claims description 3
206010027599 migraine Diseases 0.000 claims description 3
235000020824 obesity Nutrition 0.000 claims description 3
208000019906 panic disease Diseases 0.000 claims description 3
208000002271 trichotillomania Diseases 0.000 claims description 3
239000004215 Carbon black (E152) Substances 0.000 claims description 2
230000001684 chronic effect Effects 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
150000002430 hydrocarbons Chemical class 0.000 claims description 2
239000012452 mother liquor Substances 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
229940079593 drug Drugs 0.000 claims 2
125000001033 ether group Chemical group 0.000 claims 2
201000009032 substance abuse Diseases 0.000 claims 2
208000000094 Chronic Pain Diseases 0.000 claims 1
150000001298 alcohols Chemical class 0.000 claims 1
238000004090 dissolution Methods 0.000 claims 1
150000002170 ethers Chemical class 0.000 claims 1
239000000047 product Substances 0.000 description 19
238000001914 filtration Methods 0.000 description 14
239000012299 nitrogen atmosphere Substances 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
239000007787 solid Substances 0.000 description 7
238000010992 reflux Methods 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000004480 active ingredient Substances 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
208000035475 disorder Diseases 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000009472 formulation Methods 0.000 description 3
238000002560 therapeutic procedure Methods 0.000 description 3
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
230000001430 anti-depressive effect Effects 0.000 description 2
239000000935 antidepressant agent Substances 0.000 description 2
229940005513 antidepressants Drugs 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
208000020401 Depressive disease Diseases 0.000 description 1
206010013654 Drug abuse Diseases 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
-1 aceonitrile Chemical compound 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000000648 anti-parkinson Effects 0.000 description 1
239000000939 antiparkinson agent Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003086 colorant Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000007906 compression Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005538 encapsulation Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
238000012994 industrial processing Methods 0.000 description 1
238000009413 insulation Methods 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000012466 permeate Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229940127557 pharmaceutical product Drugs 0.000 description 1
XHNUMAXRQGMHKZ-CVDCTZTESA-N phenyl (3s,4r)-3-(1,3-benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidine-1-carboxylate Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CN(C(=O)OC=2C=CC=CC=2)CC1 XHNUMAXRQGMHKZ-CVDCTZTESA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000009331 sowing Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
208000011117 substance-related disease Diseases 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Medicinal Chemistry (AREA)
Biomedical Technology (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Epidemiology (AREA)
Psychology (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Steroid Compounds (AREA)

ES99973027T 1998-11-30 1999-11-30 Solvatos mixtos de paroxetina-propan-2-ol. Expired - Lifetime ES2211232T3 (es)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GBGB9826182.9A GB9826182D0 (en)	1998-11-30	1998-11-30	Novel process
GB9826182		1998-11-30
GB9916257		1999-07-12
GBGB9916257.0A GB9916257D0 (en)	1999-07-12	1999-07-12	Novel compounds

Publications (1)

Publication Number	Publication Date
ES2211232T3 true ES2211232T3 (es)	2004-07-01

Family

ID=26314751

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ES99973027T Expired - Lifetime ES2211232T3 (es)	1998-11-30	1999-11-30	Solvatos mixtos de paroxetina-propan-2-ol.

Country Status (9)

Country	Link
EP (2)	EP1408039A3 (de)
JP (1)	JP2002531452A (de)
AT (1)	ATE255577T1 (de)
AU (1)	AU1397900A (de)
DE (1)	DE69913377T2 (de)
DK (1)	DK1135383T3 (de)
ES (1)	ES2211232T3 (de)
PT (1)	PT1135383E (de)
WO (1)	WO2000032594A1 (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL1017421C2 (nl)	2001-02-21	2002-01-15	Synthon Bv	Werkwijze voor het vervaardigen van paroxetine.
WO2007054978A2 (en) *	2005-11-10	2007-05-18	Jubilant Organosys Limited	Process for preparing paroxetine hydrochloride hemihydrate

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1422263A (en) *	1973-01-30	1976-01-21	Ferrosan As	4-phenyl-piperidine compounds
GB8430581D0 (en) *	1984-12-04	1985-01-09	Ferrosan As	Treatment
EP0223403B1 (de) *	1985-10-25	1993-08-04	Beecham Group Plc	Piperidinderivat, seine Herstellung und seine Verwendung als Arzneimittel
AR001982A1 (es) *	1995-02-06	1998-01-07	Smithkline Beecham Plc	Clorhidrato de paroxetina anhidratado, y procedimiento para su preparacion
EP1394160A1 (de) *	1996-06-13	2004-03-03	SUMIKA FINE CHEMICALS Co., Ltd.	Verfahren zur Herstellung von kristallinem Paroxetin-Hydrochlorid
HU221921B1 (hu) *	1996-07-08	2003-02-28	Richter Gedeon Vegyészeti Gyár Rt.	N-benzil-piperidin- és tetrahidropiridinszármazékok és eljárás azok előállítására

1999
- 1999-11-30 EP EP03078795A patent/EP1408039A3/de not_active Withdrawn
- 1999-11-30 AT AT99973027T patent/ATE255577T1/de active
- 1999-11-30 AU AU13979/00A patent/AU1397900A/en not_active Abandoned
- 1999-11-30 WO PCT/GB1999/003993 patent/WO2000032594A1/en not_active Ceased
- 1999-11-30 EP EP99973027A patent/EP1135383B1/de not_active Expired - Lifetime
- 1999-11-30 PT PT99973027T patent/PT1135383E/pt unknown
- 1999-11-30 DK DK99973027T patent/DK1135383T3/da active
- 1999-11-30 JP JP2000585236A patent/JP2002531452A/ja not_active Withdrawn
- 1999-11-30 ES ES99973027T patent/ES2211232T3/es not_active Expired - Lifetime
- 1999-11-30 DE DE69913377T patent/DE69913377T2/de not_active Expired - Lifetime

Also Published As

Publication number	Publication date
PT1135383E (pt)	2004-04-30
EP1408039A3 (de)	2004-05-12
WO2000032594A1 (en)	2000-06-08
EP1135383B1 (de)	2003-12-03
DE69913377D1 (de)	2004-01-15
EP1135383A1 (de)	2001-09-26
AU1397900A (en)	2000-06-19
EP1408039A2 (de)	2004-04-14
JP2002531452A (ja)	2002-09-24
ATE255577T1 (de)	2003-12-15
DK1135383T3 (da)	2004-04-05
DE69913377T2 (de)	2004-12-30

Publication	Publication Date	Title
EP0808314B1 (de)	2002-06-12	Formen von paroxetin hydrochlorid
US5872132A (en)	1999-02-16	Form of paroxetine hydrochloride anhydrate
EP0970955B1 (de)	2000-08-02	Paroxetinmethansulfonat
EP4530283A1 (de)	2025-04-02	Salze organischer verbindungen
JP2005501074A (ja)	2005-01-13	パロキセチン・グリチルリチン酸塩
CN111108091A (zh)	2020-05-05	维兰特罗三苯乙酸盐的新结晶形式及其制备方法
ES2211232T3 (es)	2004-07-01	Solvatos mixtos de paroxetina-propan-2-ol.
EP1137636A1 (de)	2001-10-04	Verfahren zur herstellung von paroxetinmaleat
US20030203937A1 (en)	2003-10-30	Novel compound
ES2251038T3 (es)	2006-04-16	Metodo para la cristalizacion de un derivado de tetrahidropiridina y formas cristalinas asi obtenidas.
WO2000032595A1 (en)	2000-06-08	Process for the production of paroxetine hydrochloride acetone solvate
WO2000078752A1 (en)	2000-12-28	Process for the production of paroxetine hydrochloride
EP1133492A1 (de)	2001-09-19	Verfahren zur herstellung von paroxetin hydrochlorid
CZ20004924A3 (cs)	2001-06-13	Methansulfonat paroxetinu
IES83541Y1 (en)	2004-08-11	Paroxetine methanesulfonate
WO2001025230A1 (en)	2001-04-12	Process for the preparation of paroxetine hydrochloride acetone solvate
CA2456233A1 (en)	2003-03-13	Paroxetine isethionate salt, process of preparation and use in the treatment of depression